Re: milwaukee to gulf of mex
you drop the mast to the deck in Chicago and turn back into a sailboat once you hit the Gulf. I have also read where some people drop the mast, ship it to the Gulf and step the mast when they get there.
Pretty funny, but I know personally of two contributing members here; one that has already responded to this thread and each did it differently just as you described.
Xort and Chris dropped and trucked while Porfin carried his on deck.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White